"I knew he was being held back in San Antonio. I was held back my first two years there, so I knew he was being held back," Jackson said on ESPN's The Jump when asked if Leonard's postseason ascent was a surprise. "I knew he could do these things. We are talking about a Finals MVP. Going to Toronto was great for him."
Leonard is averaging 31.2 points, 8.2 rebounds and 3.5 assists per game during the 2019 playoffs while leading the Raptors to within one game of the Eastern Conference Finals. He's been arguably the MVP of the entire playoffs, putting together an efficient, virtuoso run on both ends of the floor.
The situation was a complete 180 from last year's postseason when Leonard was with the Spurs. There was near-constant speculation about whether Leonard would return from a quadriceps injury, with the All-Star facing criticism from outsiders and coach Gregg Popovich. The handling of the injury was among the reasons Leonard requested a trade from San Antonio this summer.
Jackson said Leonard never quite fit in with the buttoned-down nature of the Spurs organization.
"I was kind of an outsider when I was there, and felt that same type of way," Jackson said. "He didn't want to go down that straight path—he wanted to wear his braids and do stuff a little different."
Leonard is famously tight-lipped with the media, so we may never know how comfortable he was in the Spurs organization. His reserved nature, from an outsider's perspective, seemed almost perfectly Spursian. Tim Duncan spent an entire career carving a legacy as arguably the greatest player of his generation while rarely giving noteworthy soundbites.
If anything, Leonard seemed to be the perfect candidate for a passing of the torch.
Jackson's quote goes to show that we only actually know what the players tell us. There is enough behind-the-scenes reporting now on Leonard to indicate some falling-out, though there didn't appear to be any issues before the 2017-18 season. Jackson hasn't played in San Antonio since 2013, but judging by his take on the Kawhi situation, it seems there was a discomfort that festered long before the falling out.